Best Resorts in St. Michaels

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 1 Resorts in St. Michaels with updated reviews, rates, and availability.

Hyatt Regency Chesapeake Bay
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers

Hyatt Regency Chesapeake Bay

4.0 star property
8.8 out of 10, Excellent, (1000)
"Perfect place for a quiet retreat. Our family had a wonderful stay. "
The price is $275
includes taxes & fees
$242 per night
May 6 - May 7
Hyatt Regency Chesapeake Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in St. Michaels
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in St. Michaels

Inn at Perry Cabin
Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (344)
"Very enjoyable stay."
The price is $604
includes taxes & fees
$549 per night
May 4 - May 5
Inn at Perry Cabin
St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1002)
"Close to our home! Nice events in St. MICHAELS, greta breakfast, kind staff!!!"
The price is $155
includes taxes & fees
$141 per night
May 4 - May 5
St Michaels Inn
The Wildset
Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (311)
"We loved staying here and would recommend this hotel to anyone. It was so clean, convenient to all the shops,and restaurants and we loved all the little touches like breakfast, the bikes, and the nightly s'mores."
The price is $263
includes taxes & fees
$239 per night
May 4 - May 5
The Wildset
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What is St. Michaels like for a resort vacation?
You deserve a vacation, and a resort is just the place to treat yourself to the services and amenities you need for a relaxing trip to St. Michaels. One of the comfortable resorts in the area might be just what you’re searching for, whether you want a luxurious suite, blissful spa treatments, or nightly entertainment options.
What's the best resort for my stay in St. Michaels?
Our highest-rated resort near St. Michaels: Hyatt Regency Chesapeake Bay - Beach resort. 18.2 mi (29.3 km) from St. Michaels. Features 2 outdoor pools, 3 restaurants, and a private beach. Popular for its pool.
What can I do in St. Michaels?
Travelers enjoy visiting the historic sites and other landmarks in St. Michaels, and have good things to say about activities such as shopping. Check out the interesting exhibits at Chesapeake Bay Maritime Museum, or discover the shopping possibilities at Saint Michaels Village. St. Michaels Winery and St. Michaels Marina are a few additional attractions in the area that you might like.
What's the weather like in St. Michaels?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for St. Michaels is 53 inches.
What's the best way to get to and around St. Michaels?
Fly into Easton, MD (ESN-Easton - Newnam), which is located 8.8 mi (14.1 km) from the city center. Otherwise, look for flights into Fort Meade, MD (FME-Tipton), which is 35.5 mi (57.2 km) away. If you’d like to explore around the area, you may want a rental car for your journey.